A father recounts his involvement with his sons' IT careers beginning around 2012. His three sons secured jobs at a promising web project with significant VIP backing. They later asked their father to invest in the project, which he did. The project launched late, over budget, and incomplete. The CEO then brought the father in to fix the issues, which he successfully did. During his time there, he discovered bids for the project ranged from $5,000 to higher amounts, with one vendor planning to outsource cheap labor from India. After restoring functionality, the CEO declared the project should be rewritten in PHP, inspired by Facebook's alleged use of the language. A meeting followed to estimate the rewrite duration, with most suggesting only a few weeks. The father, however, provided a realistic estimate of at least seven months. Consequently, he was let go for not being "forward-thinking enough." His sons remained for another year, reporting on the extended PHP rewrite. The author uses this experience to illustrate that the most experienced individuals often provide the most accurate, albeit less popular, time and cost estimates. He then invites others to share their own intergenerational workplace oddities.